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Phthalocyanine-hydrotalcite complex and preparation method and application thereof

The technology of hydrotalcite and composite is applied in the field of phthalocyanine-hydrotalcite composite photosensitizer and its preparation, and achieves the effects of strong ability to penetrate biological membranes, high biocompatibility and easy industrialization

Active Publication Date: 2014-04-30
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on hydrotalcite as a photodynamic drug carrier has not been reported in the literature.

Method used

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  • Phthalocyanine-hydrotalcite complex and preparation method and application thereof
  • Phthalocyanine-hydrotalcite complex and preparation method and application thereof
  • Phthalocyanine-hydrotalcite complex and preparation method and application thereof

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preparation example Construction

[0042] The preparation method of phthalocyanine-hydrotalcite compound of the present invention comprises the following steps:

[0043] Prepare aqueous solutions containing divalent metal salts and trivalent metal salts, lye (sodium hydroxide or potassium hydroxide aqueous solution), and phthalocyanine aqueous solution. Under the protection of nitrogen, slowly add metal salt solution and lye dropwise to the phthalocyanine aqueous solution, and stir at 15~30°C for 0.5~2h. Afterwards, the temperature was raised to 50~70°C, and the stirring reaction was continued for 1~3h. After the crude product is centrifuged, washed and hydrothermally treated, a phthalocyanine-hydrotalcite complex can be obtained.

[0044] In the above reaction, in the metal salt aqueous solution, the concentration of divalent metal ions is 0.1~0.5 mol / L, and the concentration of trivalent metal ions is 0.025~0.25 mol / L; in the lye, the concentration of hydroxide is 0.1~2 mol / L; in the phthalocyanine aqueous...

Embodiment 1

[0051] Synthesis and Physicochemical Properties of Zinc Tetra-a-(6,8-disulfo-2-naphthyloxy)phthalocyanine

[0052]

[0053] Formula 1)

[0054] This compound can also be called 1,8(11), 15(18), 22(25)-tetrakis(6,8-disulfonic acid group-2-naphthyloxy)zinc phthalocyanine, and its structure is as formula (1 ), where:

[0055] .

[0056] (1) Preparation of 3-(6,8-disulfonic acid-2-naphthyloxy) phthalonitrile dipotassium salt: with 3-nitrophthalonitrile (5 mmol) and 2-naphthol-6, Dipotassium 8-disulfonate (5~7.5mmol, preferably 5mmol) was used as reactant, dimethyl sulfoxide (10~25mL, preferably 10mL) was used as solvent, in potassium carbonate (7.5~15mmol, preferably 10mmol), divided into three In the presence of batch addition) and nitrogen protection, the reaction was stirred at room temperature to 45°C (preferably 45°C) for 48 to 96 hours, monitored by thin-layer chromatography, and the reaction was terminated when 3-nitrophthalonitrile was basically consumed. Filter t...

Embodiment 2

[0061] Synthesis and Physicochemical Properties of Zinc Tetra-a-(4-sulfo-phenoxy)phthalocyanine

[0062] This compound can also be called 1,8(11), 15(18), 22(25)-tetrakis(4-sulfonic acid group-phenoxy)zinc phthalocyanine, and its structure is shown in formula (1), wherein :

[0063] .

[0064] (1) Preparation of 3-(4-sulfonic acid-phenoxy) phthalonitrile sodium salt: 3-nitrophthalonitrile (5mmol) and 4-hydroxybenzenesulfonate sodium (5~7.5 mmol, Preferably 5mmol) as the reactant, dimethyl sulfoxide (10~25mL, preferably 10mL) as the solvent, in the presence of potassium carbonate (7.5~15mmol, preferably 10mmol, added in three batches) and under nitrogen protection, at room temperature~45°C Stir the reaction at 45°C (preferably 45°C) for 48-96 hours, monitor by thin-layer chromatography, terminate the reaction when the 3-nitrophthalonitrile is basically consumed, remove the insoluble matter by suction filtration after the reaction, add 30ml ice chloroform to the filtrate , ...

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Abstract

The invention discloses a phthalocyanine-hydrotalcite complex and a preparation method and application thereof, and belongs to the field of inorganic-organic composite functional materials and preparation of photodynamic drugs. The complex consists of hydrotalcite and phthalocyanine, wherein the hydrotalcite electrostatically interacts with phthalocyanine; the phthalocyanine is insercalated between hydrotalcite layers, or is adsorbed to the surface of hydrotalcite; the weight percent of phthalocyanine in the complex is 0.01 to 50. The complex forms stable nanoparticles in a physiological solution, and is high in biocompatibility and photostability; the fluorescent performance and photodynamic activity of the complex are sensitive to the pH value of a system, so that the complex can be used as a targeted photosensitizer responsive to a tumor slightly-acid environment.

Description

Technical field [0001] The present invention is an inorganic-organic composite functional material and optical power drug preparation field, which involves a kind of sensitive 酞 酞-water talcum composite light sensitrant and its preparation method. Background technique [0002] 类 酞 酞 is an important functional material that has important applications in the fields of dyes, optical record medium, non -linear optical materials, catalysts, etc. Among them, the 酞 酞 酞 as a photoresistid agent in Photodynamic therapy)The prospect attracted attention. [0003] The so -called photovoltaic therapy (or optical power therapy), in essence, is the application of photovoltaic reactions of photoresistid agent (or optical drugs) in the medical field.The process is that the optical agent is injected into the body first, and after a period of time (this waiting time is to make the drug relatively rich in the target body), the light shooting target with a specific wavelength (the target in the body ...

Claims

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Application Information

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IPC IPC(8): C07D487/22C09K11/06A61K31/555A61K47/02A61K41/00A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P9/10A61P17/02A61P17/00A61P31/12A01N43/90A01P1/00A61L2/18C02F1/30A61L101/44
CPCA61K41/0071A61K47/52
Inventor 黄剑东李兴淑柯美荣唐庆庆
Owner FUZHOU UNIV
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